1,2-Dichloroethane → HCID 86679596, compound

HRID 1776653Notes

Reaction equation

HRID 1776653 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][N:7]=1)(=[O:4])=[O:3].[Cl:15][C:16]1[CH:17]=[N+:18]([O-:45])[CH:19]=[C:20]([Cl:44])[C:21]=1[CH2:22][C@@H:23]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:38])[F:37])=[C:31]([O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[CH:30]=1)[O:24][C:25](=[O:28])[CH2:26]O.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:44][C:20]1[CH:19]=[N+:18]([O-:45])[CH:17]=[C:16]([Cl:15])[C:21]=1[CH2:22][C@@H:23]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:38])[F:37])=[C:31]([O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[CH:30]=1)[O:24][C:25](=[O:28])[CH2:26][O:13][C:12]([C:9]1[CH:8]=[N:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[N:11][CH:10]=1)=[O:14]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 86679512(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxideHCID 866795972-(Methylsulfonamido)pyrimidine-5-carboxylic acid

Product 1

HCID 86679596HCID 86679596, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(methylsulfonamido)pyrimidine-5-carboxylic acid (0.130 g, 0.599 mmol) in dry DCM (5.44 ml), (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxide (See Scheme 21, step 6-9) (0.260 g, 0.544 mmol), EDC (0.313 g, 1.632 mmol), and DMAP (0.665 g, 0.544 mmol) were sequentially added with stirring at room temperature under nitrogen, and the mixture was stirred for 20 hours. The solvent was removed, and the crude was purified by flash chromatography on silica gel column (DCM:MeOH=97:3 to 95:5) affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(2-(methylsulfonamido)pyrimidine-5-carbonyloxy)acetoxy)ethyl)pyridine 1-oxide as a pale yellow spongy solid (0.168 g, 0.248 mmol, 45.6% yield, MS/ESI+ 677.1 [MH]+, [αD]=−47.48, c=0.5, MeOH).

Workup

  1. additionwere sequentially added
  2. stirringthe mixture was stirred for 20 hours
  3. customThe solvent was removed
  4. customthe crude was purified by flash chromatography on silica gel column (DCM:MeOH=97:3 to 95:5)

Sources & evidence

ORD record
ord-99c7c3f88e5146fdb8ac66515e294c41
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…